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Lab 14: Qualitative Organic Analysis

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Lab 14: Qualitative Organic Analysis Written by Danielle M. Solano Department of Chemistry & Biochemistry California State University, Bakersfield Objectives By the end of this laboratory, you should have developed the skills to do the following: • Determine the functional group of an unknown compound by using classification tests. • Understand the purpose of a synthetic derivative. Background Organic chemists often must identify unknown compounds. In some cases, such as a reaction, you may have a good idea of what the compound in question is. However in other cases, such as when you isolate a compound from a natural source, you may have no idea what the compound might be. In this experiment you will determine the identity of an unknown compound. First, you will need to purify your compound, then you will need to identify its functional group (it will contain only one), and finally you will need to make a derivative of the compound. You will confirm your results with boiling or melting point, IR, and NMR. Impurities in your compound will make it extremely difficult to identify. Thus, before you do anything else, you will need to make sure your unknown compound is pure. Consider each of the following purification techniques you have learned over the course of the year. 1. Recrystallization: Works well for solid compounds. You will need to find an appropriate recrystallization solvent. Consider a variety of solvents and mixed solvent systems. 2. Distillation: Works well for liquids that have a boiling point of <250 °C. (Note: Fractional distillation may be required if you suspect impurities close to the boiling point of your unknown.) 3. Column Chromatography: Works well for UV active compounds. You will need to use TLC to identify a solvent system that will separate your unknown from any impurities. After you have purified your unknown, verify that it is pure enough to proceed by measuring the boiling or melting point. Note that while you will not know what the melting point or boiling point of your unknown should be, the narrowness is an excellent indicator of whether or not your product is pure. Also pay attention to the appearance of your unknown and see if it has changed (hopefully for the better) during the course of the purification process. Once your unknown is pure, you will need to identify its functional group. Your unknown will have one major functional group (alcohol, ketone, aldehyde, amide, amine, carboxylic acid, or ester). Additionally, your unknown compound may or may not contain an aromatic ring. To determine the _____________________________________________________________________________________ 1 Lab 14: Qualitative Organic Analysis functional group, it is recommended that you start with solubility tests, and then conduct functional group classification tests. IR spectroscopy may also be useful at this point. Solubility can sometimes provide a surprisingly useful amount of information. First, you will test your unknown’s solubility in water. Compounds with 4 carbons or less will easily dissolve in water, whereas compounds with 8 carbons or more will be insoluble. Compounds containing 5-7 carbons may or may not dissolve (often they will display “partial” solubility). If your compound dissolves in water, you will also want to check the pH of the solution. Amines will typically be basic, and carboxylic acids will typically be acidic. Most other compounds will be neutral. Compounds that are insoluble in water should then be subjected to a solubility test in 5% HCl. Typically, only amines will be soluble in HCl because they form water-soluble hydrochloride salts when they react with HCl. Compounds that are not soluble in HCl, should be subjected to testing in basic solutions (5% NaOH and 5% NaHCO3). Both strong and weak acids (Carboxylic acids and phenols) will be deprotonated by NaOH to form water-soluble alkoxides. Only strong acids like carboxylic acids will react with NaHCO3. Compounds that are not soluble in base should then be reacted with a very strong acid, sulfuric acid (note that in the case of sulfuric acid, “solubility” is also indicated by any type of reaction such as heat, gas generation, or a color change). Compounds that cannot become protonated by sulfuric acid at all (i.e., alkanes, alkyl halides, and aromatic carbons) will still remain insoluble. These solubility tests are summarized in the flow charts below. pH > 8 Low MW basic (i.e., amines) Water Soluble pH 5-8 Low MW neutral (contains an N or O) Compounds pH < 5 Low MW acidic (i.e., carboxylic acids) Soluble in 5% HCl High MW basic (i.e., amines) Soluble in 5% NaHCO High MW strongly acidic Water Insoluble Soluble in 3 (i.e., carboxylic acids) Compounds 5% NaOH Insoluble in Insoluble in 5% NaHCO3 High MW weakly acidic 5% HCl (i.e., phenols) Soluble in H SO Insoluble in 2 4 High MW Neutral 5% NaOH (contains an N or O) Insoluble in H2SO4 High MW Neutral (does not contain an N or O) The results from the solubility tests can significantly help in determining which classification tests should then be performed, or at least narrow down the list. By no means do you need to conduct all classification tests. In fact, you should do your best to select only tests that will provide you with additional information about your unknown and/or confirm results. Also, make sure that your glassware is clean and dry so you do not get any false positive or false negative results. Keep in mind that a negative result for a classification test provides useful information, so be sure to keep track of negative results as well as positive results. Also, for each classification test that you _____________________________________________________________________________________ 2 Lab 14: Qualitative Organic Analysis perform, be sure to run a blank, and one or more controls. These will help you to determine if a reaction actually occurred. A blank includes everything but the unknown, and a control includes a compound for which the outcome is known in place of the unknown. Controls can be positive (a compound you know will react) or negative (a compound that you know will not react). The classification tests are summarized in the table below. Functional Group Test Test No. Notes Alcohols Acetyl chloride C-1 Tests for the presence of alcohols Tests for the presence of 1° alcohols, 2° Chromic acid C-9 alcohols, & aldehydes Tests for –CH(OH)CH and –COCH Iodoform test C-16 3 3 groupings Lucas’s test C-17 Used to classify alcohols as 1°, 2°, or 3° Aldehydes Benedict’s test C-6 Tests for the presence of aldehydes Tests for the presence of 1° alcohols, 2° Chromic acid C-9 alcohols, & aldehydes Tests for the presence of aldehydes & 2,4-Dinitrophenylhydrazine C-11 ketones Tollen’s test C-23 Tests for the presence of aldehydes Amides Alkaline hydrolysis C-2 Tests for the presence of amides & esters Tests for the presence of nitrogens and Elemental analysis C-12 halogens Used to distinguish alkyl amines from Amines Basicity test C-4 aromatic amines Tests for the presence of phenols & Bromine water C-8 aromatic amines Tests for the presence of nitrogens and Elemental analysis C-12 halogens Hinsberg’s test C-15 Used to classify amines as 1°, 2°, or 3° Quinhydrone C-20 Used to classify amines as 1°, 2°, or 3° Aromatics Aluminum chloride & chloroform C-3 Tests for the presence of aromatic rings Provides information about the number of Carboxylic Acids Neutralization equivalent C-18 carboxylic acids and the MW Esters Alkaline hydrolysis C-2 Tests for the presence of amides & esters Ferric hydroxamate C-14 Tests for the presence of esters Tests for the presence of aldehydes & Ketones 2,4-Dinitrophenylhydrazine C-11 ketones Tests for –CH(OH)CH and –COCH Iodoform test C-16 3 3 groupings Tests for the presence of phenols & Phenols Bromine water C-8 aromatic amines Ferric chloride C-13 Tests for the presence of phenols _____________________________________________________________________________________ 3 Lab 14: Qualitative Organic Analysis At this point, you should be able to use your boiling or melting point data combined with the results of your functional group data to develop a hypothesis as to what your unknown might be or at least narrow down the list to only a few candidates. Note that due to the accuracy (or lack thereof) of our thermometers, your boiling or melting points may be up to 15 °C lower than the literature values. Once your functional group has been determined, you will prepare a derivative of your unknown. To prepare a derivative, you will select a suitable reaction that converts your unknown into a different functional group for which the boiling or melting point is known. This is particularly useful because compounds that have similar boiling or melting points will often have derivatives that differ significantly in terms of boiling or melting point. You should then be able to identify your unknown using this information. Finally, you can confirm the identity of your product using IR and NMR. Note that these measurements can be taken at anytime during the course of the lab after you purified your product. In fact, it is recommended that you conduct them sooner rather than later as they may provide valuable information as to the identity of your unknown (e.g., IR may reveal your functional group). Lab Notebook Preparation A Before coming to lab on the first day of this experiment, the following items must be in your lab notebook: 1. Title of experiment 2. Date the experiment is to be performed 3. Outline of your plan for determining the identity of your unknown 4. Hazards of and appropriate precautions for the safe handling of unknown organic compounds 5.
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